5-Methyl-alpha[(methylthio)methyl]-2-furan acrolein

ABSTRACT

Processes and compositions are described for use in foodstuff flavors and as foodstuff article aroma and taste augmenting and enhancing materials of at least one alpha-substituted alkylidene methionals having the structure: ##STR1## wherein R 1  or R 2  is one of the moieties: ##STR2## AND THE OTHER IS HYDROGEN OR METHYL. Addition of one or more alpha-substituted alkylidene methionals to foodstuff flavorings or to foostuffs is indicated to produce the following aroma and flavor characteristics, in the alternative taken together: 
     Aroma 
     Potato; Methional-like; Green; Hydrolyzed vegetable protein-like; Chicken-like; Cabbage; Green potato; Green weedy; Broccoli-like; and Green bean-like. 
     Flavor 
     Potato; Metallic; Sulfury-green; Cabbage-like; Chicken; Mushroom-like; Green-weedy; Broccoli-like; and Green bean-like. The compounds of our invention are useful in augmenting or enhancing the flavor and aroma nuances of vegetable (including potato and cabbage) and chicken flavors.

This is a divisional of application Ser. No. 753,462, filed Dec. 22,1976, now U.S. Pat. No. 4,064,279.

BACKGROUND OF THE INVENTION

The present invention relates to alpha-substituted alkylidene methionalsand novel compositions using such compounds to augment or enhance theflavor and/or aroma of foodstuffs.

There has been considerable work performed relating to substances usefulin augmenting or enhancing the flavor and/or aroma of variuos consumablematerials including foodstuffs. These substances are used to supplementthe use of natural materials, some of which may be in short supplyand/or provide more uniform properties in the finished product. Thefollowing flavor and aroma notes are desirable, particularly invegetable (including potato and cabbage) and chicken flavoredfoodstuffs:

Aroma

Potato; Methional-like; Green; Hydrolyzed vegetable protein-like;Chicken-like; Cabbage; Green potato; Green weedy; Broccoli-like; andGreen bean-like.

Flavor

Potato; Metallic; Sulfury-green; Cabbage-like; Chicken; Mushroom-like;Green-weedy; Broccoli-like; and Green bean-like.

2,8-DITHIANON-4-ENE-4-CARBOXALDEHYDE HAVING THE STRUCTURE: ##STR3## hasbeen isolated from hydrolyzed vegetable protein distillate and has beenfound to have a sweet, meaty, hydrolyzed vegetable protein taste at 0.02ppm, the threshold level. At 0.5 ppm2,8-dithianon-4-ene-4-carboxaldehyde has a liver sausage, cabbage,potato, metallic, hydrolyzed vegetable protein-like, beef broth andmethional aroma with liver sausage, cabbage, potato, hydrolyzedvegetable protein-like, beef broth-like, limburger cheese-like andmethional-like flavor. The compound naturally-occurring in hydrolyzedvegetable protein distillate, has flavor and aroma nuances many of whichare different in kind from the flavor and aroma nuances of the compoundsof this invention.

Buttery, in an article entitled "Some Unusual Volatile CarbonylComponents of Potato Chips", J. Agr. Food Chem., Vol. 21, No. 1, 1973,pages 31-33, discloses compounds having the structures: ##STR4## Thecompounds disclosed by Buttery are considered to have structuresdifferent in kind from the structures of the compounds of the instantinvention. Furthermore, the flavor and aroma nuances of these compoundsof Buttery are different in king from the flavor and aroma nuances ofthe compounds of the instant invention.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1A illustrates the GLC spectrum for2-[(methylthio)methyl]-3-phenyl-2-propenal produced according to ExampleI.

FIG. 2A illustrates the Mass Sprectrum for2-[(methylthio)methyl]-3-phenyl-2-propenal produced according to ExampleI.

FIG. 1B illustrates the GLC spectrum for the neutral fraction containing2,8-dithianon-4-ene-4-carboxaldehyde.

FIG. 2B illustrates the Mass Spectrum for the neutral fractioncontaining 2,8-dithianon-4-ene-4-carboxaldehyde.

FIG. 3 illustrates the NMR spectrum for the compound produced accordingto Example II.

FIG. 4 illustrates the Infrared spectrum for the compound producedaccording to Example II.

FIG. 5 illustrates the Mass Spectrum for the compound produced accordingto Example II.

FIG. 6 illustrates the Mass Spectrum for the compound produced accordingto Example III.

FIG. 7 illustrates the NMR spectrum for the compound produced accordingto Example IV.

FIG. 8 illustrates the Infrared spectrum for the compound producedaccording to Example IV.

THE INVENTION

The present invention comprises novel compositions and foodstuffscontaining alpha-substituted alkylidene methionals having the structure:##STR5## wherein R₁ or R₂ is one of the moieties: ##STR6## and the outeris hydrogen or methyl, the specific embodiments of which are describedhereinafter by way of example and in accordance with which it is nowpreferred to practice the invention.

Such alpha-substituted alkylidene methionals are obtained by reacting analdehyde or a methyl ketone with methional in the presence of a baseaccording to the following reaction: ##STR7## wherein R₁ and R₂ are asdefined as above. This reaction takes place in the presence of a basesuch as alkali metal hydroxide or an alkali earth metal hydroxide. Thereaction is well known as an "aldol condensation" type reaction.Examples of base which can be used in this reaction are lithiumhydroxide, sodium hydroxide, potassium hydroxide and barium hydroxide.The concentration of base may vary between 0.1 molar up to 5 molar witha preferred concentration range of from 0.3 molar up to 0.8 molar. Thereaction temperature range is between -10° and 50° C with a temperatureof reaction being a function of the particular base catalyst used.

The mole ratio of methional to methyl ketone or aldehyde is notcritical, but most convenient is a mole ratio of 1:1.

At the end of this invention the reaction mass is "worked by" byextracting the reaction product with a solvent such as methylenechloride and then treating the organic layer with weak acid and weakbase and finally fractionally distilling the resulting reaction product,e.g., by means of vacuum distillation.

Specific examples of alpha-substituted alkylidene methionals producedusing the afore-mentioned process and their food flavor properties areas follows (as set forth in Table I below):

                  Table I                                                         ______________________________________                                        Compound  Structure        Flavor Property                                    ______________________________________                                        2-[(methyl- thio)methyl]- 3-phenyl- 2-propenal                                           ##STR8##        A green weedy, broccoli-like, green bean-like                                 aroma with a green weedy, broccoli-like and                                   green bean- like flavor at 20 ppm.                 5-methyl- alpha[(methyl- thio)methyl]- 2-furan acrolein                                  ##STR9##        A potato-like, methional-like,  green sulfury,                                ydrolyzed vegetable protein, chicken-like,                                    cabbage, green potato-like aroma character                                    with potato-like, metallic sulfury green,                                     cabbage- like, chicken and mushroom-like                                      flavor nuances at 1ppm.                            ______________________________________                                    

The distillate of hydrolyzed vegetable protein (as produced according toExample I, infra), appears to contain the following alpha-substitutedalkylidene methionals:

2-[(methylthio)methyl]-3-phenyl-2-propenal; and

2,8-dithianon-4-ene-4-carboxaldehyde. The presence of the foregoingmaterials in the distillate of hydrolyzed vegetable protein is indicatedin various peaks in FIGS. 1A and 1B, respectively. The presence of suchcompounds in hydrolyzed vegetable protein distillate is not consideredto infer that these compounds can be used as foodstuff flavorants orthat they can be used in order to augment or enhance the flavor or aromaof a foodstuff.

When the alpha-substituted alkylidene methionals of our invention areused as food flavor adjuvants, or are used to augment or enhance theflavor or aroma characteristics of foodstuffs, the nature of theco-ingredients included with the said alpha-substituted alkylidenemethionals in formulating the product composition will also serve toaugment the organoleptic characteristics of the ultimate foodstufftreated therewith.

As used herein in regard to flavors, the term "augment" in its variousforms means "supplying or imparting flavor character or note tootherwise bland, relatively tasteless substances or augmenting theexisting flavor characteristic where a natural flavor is deficient insome regard or supplementing the existing flavor impression to modifyits quality, charactor or taste."

As used herein in regard to food flavors, the term "enhance" is usedherein to mean the intensification of a flavor or aroma characteristicor note without the modification of the quality thereof. Thus,"enhancement" of a flavor or aroma means that the enhancement agent doesnot add any additional flavor note.

As used herein the term "foodstuff" includes both solids and liquids,and ingestible materials or chewable but non-ingestible materials suchas chewing gum. Such materials usually do, but need not, havenutritional value. Thus, foodstuffs include soups, convenience foods,beverages, gelatin desserts, dairy products, candies, vegetables,cereals, soft drinks, snacks and the like.

Substances suitable for use herein as co-ingredients or flavoringadjuvants are well known in the art for such use, being extensivelydescribed in the relevant literature. Apart from the requirements thatany such materials be organoleptically compatible with thealpha-substituted alkylidene methionals, non-reactive with thealpha-substituted alkylidene methionals of our invention and"ingestibly" acceptable and thus non-toxic or otherwise non-deleterious,nothing particularly critical resides in the selection thereof.Accordingly, such materials which may in general be characterized asflavoring adjuvants or vehicles comprise broadly stabilizers,thickeners, surface active agents, conditioners, other flavorants andflavor intensifiers.

Stabilizer compounds include preservatives, e.g., sodium chloride;antioxidants, e.g., calcium and sodium ascorbate, ascorbic acid,butylated hydroxyanisole (mixture of 2 and 3tertiary-butyl-4-hydroxyanisole), butylated hydroxy toluene(2,6-di-tertiary-butyl-4-methyl phenol), propyl gallate and the like andsequestrants, e.g., citric acid.

Thickener compounds include carriers, binders, protective colloids,suspending agents, emulsifiers and the like, e.g., agar agar,carrageenan; cellulose and cellulose derivatives such as carboxymethylcellulose and methyl cellulose; natural and synthetic gums such as gumarabic, gum tragacanth; gelatin, proteinaceous materials; lipids;carbohydrates; starches, pectins and emulsifiers, e.g., mono- anddiglycerides of fatty acids, skim milk powder, hexoses, pentoses,disaccharides, e.g., sucrose corn syrup and the like.

Surface active agents include emulsifying agents, e.g., fatty acids suchas capric acid, palmitic acid, myristic acid and the like, mono- anddiglycerides of fatty acids, lecithin, defoaming and flavor-dispersingagents such as sorbitan monostearate, potassium stearate, hydrogenatedtallow alcohol and the like.

Conditioners include compounds such as bleaching and maturing agents,e.g., benzoyl peroxide, calcium peroxide, hydrogen peroxide and thelike; starch modifiers such as peracetic acid, sodium chlorite, sodiumhypochlorite, propylene oxide, succinic anhydride and the like, buffersand neutralizing agents, e.g., sodium acetate, ammonium bicarbonate,ammonium phosphate, citric acid, lactic acid, vinegar and the like;firming agents such as aluminum sodium sulfate, calcium chloride andcalcium gluconate; texturizers, anti-caking agents, e.g., aluminumcalcium sulfate and tribasic calcium phosphate; enzymes; yeast foods,e.g., calcium lactate and calcium sulfate; nutrient supplements, e.g.,iron salts such as ferric phosphate, ferrous gluconate and the like,riboflavin, vitamins, zinc sources such as zinc chloride, zinc sulfateand the like.

Other flavorants and flavor intensifiers include vanillin, ethylvanillin, diacetyl, phenethyl 2-furoate, maltol, neryl butyrate, amylbutyrate, allyl caproate, citral, 4-methylthiobutanal, 2-trans hexenal,dimethyl sulfide, linalool, acetic acid, methyl sulfide, acetaldehyde,isovaleraldehyde, isoamyl alcohol, acetic acid, lactones, includingδ-decalactone, δ-undecalactone and γ-nonalactone, isoamyl estersincluding the acetate, butyrate and octanoate, pyrazines such asdimethyl pyrazine, 2-ethyl-3-methyl pyrazine, 2-ethyl-3-methyl pyrazine,2,3-diethyl-5-methyl pyrazine, 2-ethyl-3-acetyl pyrazine, tetramethylpyrazine, 2-methyl pyrazine, amyl octanoate, benzoic acid, pyridine,phenylacetic acid, cinnamyl esters such as the propionate,4-phenyl-3-butene-2-one, 3-phenyl-2-pentenal, 3-phenyl-3-pentenal,3-phenyl-4-pentenal, 2-phenyl-2-methyl-4-pentenal, 2-phenyl-4-pentenal,2-phenyl-4-pentenal dimethyl acetal, 2-isobutylthiazole, 2-(secondarybutyl) thiazole, 2-(i-propyl) thiazole and 2-(n-propyl) thiazole. Theseare combined in proportions requisite to obtain the desired effect asillustrated further hereinbelow.

As will be appreciated by those skilled in the art, the amount ofalpha-substituted alkylidene methionals employed in a particularinstance can vary over a relatively wide range whereby to its desiredorganoleptic effects having reference to the nature of the product areachieved. Thus, correspondingly greater amounts would be necessary inthose instances wherein the ultimate food composition to be flavored isrelatively bland to the taste, whereas relatively minor quantities maysuffice for purposes of enhancing the composition merely deficient innatural flavor or aroma. The primary requirement is that the amountselected be effective, i.e., sufficient to alter the organolepticcharacteristics of the parent composition.

The use of insufficient quantities of alpha-substituted alkylidenemethionals will, of course, substantially vitate any possibility ofobtaining the desired results while excess quantities prove needlesslycostly and in extreme cases may disrupt the flavor-aroma balance, thusproving self-defeating. Accordingly, the terminology "effective amount"and "sufficient amount" is to be accorded a significance in the contextof the present invention consistent with the obtention of desiredflavoring effects.

Thus, and with respect to ultimate food compositions, it is found thatquantities of alpha-substituted alkylidene methionals ranging from asmall but effective amount, e.g., abut 0.02 parts per million up toabout 50 parts per million by weight based on total composition (morepreferably from about 0.2 ppm up to about 25 ppm) are suitable.Concentrations in excess of the maximum quantity stated are not normallyrecommended, since they fail to prove commensurate enhancement oforganoleptic properties. In those instances, wherein thealpha-substituted alkylidene methionals is added to the foodstuff as anintegral component of a flavoring composition, it is, of course,essential that the total quantity of flavoring composition employed besufficient to yield an effective alpha-substituted alkylidene methionalconcentration in the foodstuff product.

Food flavoring compositions prepared in accordance with the presentinvention preferably contain the alpha-substituted alkylidene methionalin concentrations ranging from about 0.1% up to about 15% by weightbased on the total weight of said flavoring composition.

The compositions described herein can be prepared according toconventional techniques well known as typified by cake batters and fruitdrinks and can be formulated by merely admixing the involved ingredientswithin the proportions stated in a suitable blender to obtain thedesired consistency, homogeneity of dispersion, etc. Alternatively,flavoring compositions in the form of particulate solids can beconveniently prepared by mixing the alpha-substituted alkylidenemethionals with, for example, gum arabic, gum tragacanth, carrageenanand the like, and thereafter spraydrying the resultant mixture wherebyto obtain the particular solid product. Pre-prepared flavor mixes inpowder form, e.g., a fruit-flavored powder mix, are obtained by mixingthe dried solid components, e.g., starch, sugar and the like andalpha-substituted alkylidene methionals in a dry blender until therequisite degree of uniformity is achieved.

It is presently preferred to combine with the alpha-substitutedalkylidene methionals, the following adjuvants:

Acetaldehyde;

Isobutyraldehyde;

Isovaleraldehyde;

Methyl sulfide;

Methyl disulfide;

Isobutyl acetate;

Phenylethyl acetate;

Diacetyl;

Acetophenone;

Furfural (50%);

Benzaldehyde;

Phenylacetaldehyde;

Isoamyl alcohol;

Phenylethyl alcohol;

Gamma-butyrolactone;

3-Phenyl-4-pentenal;

3-Phenyl-3-pentenal;

3-Phenyl-2-pentenal;

Methyl pyrazine;

Tetramethyl pyrazine;

Trimethylpyrazine;

2,6-Dimethylpyrazine;

2-Ethyl-3-methylpyrazine;

2-Ethyl-3,5-dimethylpyrazine;

2-Ethyl-3,6-dimethylpyrazine;

2-Ethyl-5-methylpyrazine;

2-Ethyl-3-acetyl pyrazine;

2-(i-butyl) thiazole;

2-(i-propyl) thiazole;

2-(n-propyl) thiazole;

2-Phenyl-4-pentenal;

2-Phenyl-4-pentenaldimethylacetal;

4-Methylthiobutanal;

trans-2-hexenal;

Hydrolyzed vegetable protein;

Monosodium glutamate;

Black pepper oil;

Nutmeg oil;

Celery oil;

Lemon oil;

Mustard oil.

The following examples are given to illustrate embodiments of theinvention as it is presently preferred to practice it. It will beunderstood that these examples are illustrative and that the inventionis not to be considered as restricted thereto except as indicated in theappended claims.

EXAMPLE I PREPARATION AND ANALYSIS OF DISTILLATE OF HYDROLYZED VEGETABLEPROTEIN

240 pounds of Nestle 4-BE hydrolyzed vegetable protein is intimatelyadmixed with 240 pounds deionized water. The resulting mixture ismetered into a Turbofilm evaporator and distilled under atmosphericpressure whereby 20% is recovered as an aqueous distillate and 80% isdiscarded. The aqueous distillate is then subjected to extraction in a22 liter round bottom liquid-liquid extractor. The extractor is chargedwith the aqueous distillate and saturated with sodium chloride. Theresulting mixture is extracted with diethyl ether. The ether extract isthen evaporated using a 5 liter Kuederna-Danish evaporator. Theresulting material is then fractionated into acidic, phenolic, basic andneutral components. Each of the fractions is analyzed using GLC, NMR, IRand mass spectral analyses. Evidence is obtained by the foregoinganalyses which indicate that the following alpha-substituted alkylidenemethionals may be present in the neutral fraction:

2,8-dithianon-4-ene-4-carboxaldehyde; and

2-[(methylthio)methyl]-3-phenyl-2-propenal. The GLC spectrum for theneutral fraction containing 2,8-dithianon-4-ene-4-carboxaldehyde is setforth in FIG. 1B and the MS analysis is set forth in FIG. 2B. Evidencefor 2-[(methylthio)methyl]-3-phenyl-2-propenal is set forth in the GLCspectrum of the neutral fraction in FIG. 1A and the MS analysis of thecompounds is set forth in FIG. 2A.

EXAMPLE II PREPARATION OF 5-METHYL-ALPHA-[(METHYLTHIO)METHYL]-2-FURANACROLEIN ##STR10##

Into a 1 liter reaction flask equipped with mechanical stirrer, 250 mladdition funnel, Y adaptor, thermometer and Friedrich condenser isplaced 104 grams methional and 110 grams of 5-methyl furfural. Thereaction mass is cooled to 0° C and 100 ml of a 0.5 molar solution ofsodium hydroxide is added dropwise with stirring. The reaction mass ispermitted to stir at 0° C for 2 hours. The resulting reaction mass isextracted with three 100 ml portions of methylene chloride and theextracts are combined, dried over anhydrous sodium sulfate andevaporated on a rotary evaporator. The resulting product is distilled ona short path column, boiling point 155° C (5 mm Hg).

The NMR data are as follows:

    ______________________________________                                        Chemical                                                                      Shift (ppm) Assignment     Integration                                        ______________________________________                                        2.06 (s)    CH.sub.3S      3H                                                 2.36 (s)                                                                                   ##STR11##     3H                                                 3.68 (S)    CCCH.sub.2S    2H                                                 6.06 (d, J=4H.sub.z)       1H                                                 6.62 (d, J=4H.sub.z)                                                                      Furan protons  1H                                                 6.78 (s)    Olefinic proton                                                                              1H                                                 9.26 (s)    HCO            1H                                                 ______________________________________                                    

The Infrared data are as follows:

Absorption Bands cm⁻¹ 780, 850, 1015, 1120, 1210, 1355, 1420, 1500,1570, 1615, 1665, 2910.

The Mass Spectral data are as follows:

    ______________________________________                                        m/e             Relative Intensity (%)                                        ______________________________________                                        43              53                                                            51              14                                                            65              12                                                            77              42                                                            91              34                                                            93              23                                                            105             11                                                            119             14                                                            120             22                                                            121             19                                                            149             100                                                           150             11                                                            196             62                                                            ______________________________________                                    

The NMR spectrum is set forth in FIG. 3. The Infrared spectrum is setforth in FIG. 4. The Mass Spectrum is set forth in FIG. 5.

EXAMPLE III PREPARATION OF 2,8-DITHIANON-4-ENE-4-CARBOXALDEHYDE##STR12##

Into a 1 liter reaction flask equipped with mechanical stirrer, 250 mladdition funnel, Y adapter, thermometer and Friedrich condenser isplaced 208 grams of methional. The reaction mass is cooled to 0° C and100 ml of a 0.5 molar solution of sodium hydroxide is added dropwisewith stirring. The resulting reaction mass is extracted with three 100ml portions of methylene chloride and the extracts are combined, driedover anhydrous sodium sulfate and evaporated on a rotary evaporator. Theresulting product was then subjected to vacuum distillation to give theproduct, boiling point 129° C (1 mm Hg).

The Mass Spectrum is set forth in FIG. 6.

EXAMPLE IV PREPARATION OF 2-[(METHYLTHIO)METHYL]-3-PHENYL-2-PROPENAL##STR13##

Into a 100 ml three necked reaction flask equipped with stirrer,thermometer and addition funnel is charged a solution of 0.5 grams ofpotassium hydroxide in 10 ml methanol. Benzaldehyde (10.0 grams) isadded as the mixture is cooled to 5°-10° C. Methional (10.0 grams) isthen added dropwise while maintaining the reaction temperature at 5°-10°C. The mixture is then allowed to warm to room temperature and stirredfor a period of 1 hour. Most of the solvent is evaporated at reducedpressure and the mixture is partitioned between water and ether. Theorganic layer is washed several times with water and once with saturatedbrine. The solvent is evaporated leaving a yellow oil wich is distilledto give 6.1 grams product, boiling point 104°-111° C (0.4 mm Hg).

The distillate is crystallized from ether-hexane and then recrystallizedtwice from ether to give 1.5 grams of colorless needles, melting point30.4°-31.0° C.

The NMR data is as follows:

    ______________________________________                                        Chemical Shift (ppm)                                                                         Assignment     Integration                                     ______________________________________                                        2.12 (s)       CH.sub.3 S     3H                                              3.56 (s)       ═C--CH.sub.2 --S--                                                                       2H                                              7.62-7.19 (m)  aromatic protons +                                                            olefinic protons                                                                             6H                                              9.53 (s)       HC═O       1H                                              ______________________________________                                    

The Infrared absorption bands are as follows:

cm⁻¹ 695, 740, 755, 865, 1125, 1200, 1320, 1430, 1450, 1620, 1680, 2920.

The Mass Spectral data is as follows:

    ______________________________________                                        m/e                 Relative Intensity (%)                                    ______________________________________                                        29                  22                                                        39                  24                                                        45                  22                                                        63                  18                                                        91                  28                                                        115                 100                                                       116                 93                                                        117                 56                                                        144                 44                                                        m 192               18                                                        ______________________________________                                    

The NMR spectrum is set forth in FIG. 7. The Infrared spectrum is setforth in FIG. 8.

EXAMPLE V

To a portion of a standard salad dressing,2-[(methylthio)methyl]-3-phenyl-2-propenal prepared according to ExampleIV is added at a rate of 0.10 ppm. The resulting mixture has acharacteristic broccoli/green fava bean note. The salad dressing is amixture of the following:

    ______________________________________                                        Ingredient                Parts                                               ______________________________________                                        Black pepper oil          3                                                   Nutmeg oil                3                                                   Celery oil                3                                                   Lemon oil                 3                                                   Mustard oil               1                                                   Vinegar-citric acid (50:50 mixture)                                                                     120                                                 Starch paste prepared from tapioca                                            flour-water (50:50 mixture)                                                                             300                                                 Liquid egg yolks          210                                                 Sodium chloride           7                                                   Sucrose                   10                                                  Mustard                   20                                                  Locust Bean gum           6                                                   ______________________________________                                    

EXAMPLE VI POTATO FLAVOR

A potato flavoring material is prepared by admixing the followingingredients:

    ______________________________________                                        Ingredient             Parts by Weight                                        ______________________________________                                        Diacetyl (1% solution) 0.20                                                   Furfural               0.2                                                    2-acetyl-3-ethyl pyrazine                                                     (1% solution)          1.0                                                    2-ethyl-3-methyl pyrazine                                                                            4.0                                                    methional              2.0                                                    5-methyl-alpha-[methylthio)                                                   methyl]-2-furan acrolein                                                      (prepared according to                                                        Example II)            0.2                                                    ethanol (95% food grade)                                                                             91.6                                                   ______________________________________                                    

A bench panel of five individuals compared the above formulation withone not containing any 5-methyl-alpha-[(methylthio)methyl]-2-furanacrolein but identical in all other respects. The formulations werecompared at the rate of 10 ppm in water solutions. It was concluded thatthe 5-methylalpha-[(methylthio)methyl]-2-furan acrolein imparted to theflavor a mashed potato-like taste with cabbage nuances.

What is claimed is:
 1. 5-Methyl-alpha[(methylthio)methyl]-2-furanacrolein having the structure: ##STR14##